ol049422u_si_001.pdf (9.13 MB)
Synthesis of Quaternary Amino Acids Bearing a (2‘Z)-Fluorovinyl α-Branch: Potential PLP Enzyme Inactivators
journal contribution
posted on 2004-05-27, 00:00 authored by David B. Berkowitz, Roberto de la Salud-Bea, Wan-Jin JahngProtected α-formyl amino acids, themselves available from the corresponding α-vinyl amino acids, are stereoselectively transformed into the
(Z)-configured α-(2‘-fluoro)vinyl amino acids via a three-step sequence. The route employs McCarthy's reagent, diethyl α-fluoro-α-(phenylsulfonyl)methyl phosphonate, and proceeds via the intermediate (E)-α-fluorovinyl sulfones and (E)-α-fluorovinylstannanes. The latter may either be
exploited as novel cross-coupling partners for fluorovinyl branch extension or be globally deprotected, to provide the title compounds.